Everything seemed to be running smoothly, until June 30th, 1962 when Deputy Sheriff Richard Anderson, who had warned Sinatra to stay away from his wife, a former girlfriend of his, came to pick her up. On the night Anderson stopped by the kitchen to talk with some of the help there and Sinatra came in, ran up to him and screamed at him, "What the f*** are you doing, here?" Anderson remained calm and said he was waiting for his wife, when Sinatra grabbed him and tried to throw him out, resulting in Anderson punching Sinatra so hard in the face that he couldn't perform on stage for a week

On July 17th, 1962, Anderson and his wife were driven off the road by a late model maroon convertible with California plates, driving at high speeds just near the Cal-Neva Lodge. Anderson lost control of his car, skidded off the road and smashed into a tree, killing him instantly. His wife was thrown from the car, and suffered severe broken bones and fractures. Anderson's parents are still convinced that Frank had something to do with their sons death.

A few days after Anderson was murdered, and one week before her own death, Marilyn Monroe flew to the Cal-Neva at Frank Sinatra's invitation. He told Monroe that he wanted to discuss their upcoming film together, “What a Way to Go”. Monroe didn't want to go, but was told that Bobby Kennedy would be there, which changed her mind. Sinatra’s motive for inviting Monroe was so he could assist in the Kennedys attempt to blackmail Monroe into silence over her affairs with the Kennedy brothers, by making sure Marilyn reached a point of intoxiaction that would result in her passing out so Frank could ensure prostitutes molested her, which would result in pictures being taken to use as the key item in the blackmail.

FBI photographs proved Giancana was on the property playing golf and fighting with Victor LaCroix Collins, the McGuire sisters' road manager resulting in Frank’s gambling license being revoked, for hosting black listed persons in his casino.